


Only if for a Night

by My_OTP_is_Better



Category: Supernatural
Genre: Anal Sex, Angst, Awkward Sexual Situations, Child Neglect, Childhood Trauma, Dean Has Self-Esteem Issues, Episode: s05e03 Free to Be You and Me, First Kiss, First Time, Guilt, Hurt Dean Winchester, Hurt/Comfort, Implied/Referenced Child Abuse, Implied/Referenced Underage Prostitution, Inner Dialogue, John Winchester's Bad Parenting, M/M, Mildly Dubious Consent, Mind Reading, Missing Scene, Past Prostitution, Prostitution, Repressed Memories, Self-Sacrificing Dean, Starvation, Unsafe Sex, Virgin Castiel, possible whump, slightly Out of character Castiel
Language: English
Status: Completed
Published: 2014-06-05
Updated: 2014-06-05
Packaged: 2018-01-26 23:54:43
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 7,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1707212
Author URL: https://archiveofourown.org/users/My_OTP_is_Better/pseuds/My_OTP_is_Better
Summary: <blockquote class="userstuff">
              <p>"I need your help, because you are the ONLY ONE who will help me," Cas pleaded. Dean was willing to help Cas catch an archangel, but they were going to do it his way: they were going to drive, and they most certainly were not going to spend their last night on earth "sitting quietly". No, he promised Cas he wouldn't die a virgin, so they were off to Nevada. </p>
<p>But when that went south, Dean would keep his promise - one way or another.</p>
            </blockquote>





	Only if for a Night

**Author's Note:**

  * Inspired by [Absent Fathers](https://archiveofourown.org/works/694130) by [sparxwrites](https://archiveofourown.org/users/sparxwrites/pseuds/sparxwrites). 



> This is going to be a very long note. Okay, here goes: Title taken from a song by Florence+The Machine.
> 
> Usual disclaimer: I own nothing! Kripke, et al own "Supernatural" and all associated characters.
> 
> The underage tag is exclusively for flashbacks; Dean is 30/31 years old in the majority of this fic.
> 
> My idea of what Dean looked like at 16 is different than what canon says he looked like. Imagine a cross between 17/18 year old Dean on the show, and Jensen Ackles as Ben/Alec from Dark Angel, and you'll have an idea.
> 
> Please read ALL tags (I know there are a lot of them) and if anything squicks you out, don't risk it. Your mental well-being is more important than a fic. That said, nothing gets touched upon TOO deeply except for the past prostitution. Sam and Dean had some pretty shitty living conditions, but I felt the way the narrative was set up wasn't conducive to going into extreme detail. I could have, since some of these things were based off real events, but it didn't fit here. 
> 
> Anyway: I did a LOT of research for this fic, so if you have first-hand experience or found some flaw, please let me know and I will aim to correct it. Misinformation in fan-fiction helps no one.
> 
> I tried to put as many warning tags as possible, but just know: This fic is really sad. I've desensitized myself to it by reading it so many times, but it is definitely not something you should read if you're in a good mood.
> 
> As stated in the tags, this is a missing scene fic based off of 5X03. In the course of research, I realized that the only way Dean could've brought Cas to a brothel was if they went to Nevada, as Canada's repeal on the brothel law didn't occur until 2013. (I can dig up a source if you need specifics) Driving from Maine to Nevada and back is over a thousand miles each way and would've taken considerable time. Given this, it's not unreasonable Dean would've needed a lay-over.
> 
> Dub-con tag is in reference to the past prostitution. I hope the Dean/Cas scene doesn't read that way, but it's possible it might. Just know that both Dean and Cas are fully consenting to each other.
> 
> Okay, I think that's everything. Have at it.

 

“Let me tell you something. There are two things I know for certain: One, Bert and Ernie are gay; Two, you are _not_ gonna die a virgin. Not on _my_ watch,” Dean stated to a confused Castiel. Cas was sitting around a dusty table in a dilapidated shack, having just returned from Jerusalem with a container of holy oil. Dean, who had been shrugging on his jacket, started walking towards the door, hitting the back of Cas’ chair on the way.

“Let’s go,” Dean said. After several hours of driving (during which Dean caught Cas up on the whole “separate vacations” thing), they eventually arrived at a whore house.

\---------

“Hey,” he barked, getting Cas to look at him. “ _Relax_ ,” Dean ordered, after taking a sip of his beer.

“This is a _den_ of _iniquity_. I should not be here,” Cas observed quietly, eyes wide as he leaned across the table. His hands gripped the edge of the table tightly, and he swallowed uncomfortably.

Dean knit his eyebrows. “Dude, you full-on _rebelled_ against heaven. Iniquity is one of the _perks_ ,” Dean explained pointedly. A blonde in rosy lipstick and a white push-up negligee with matching high heels sauntered over, and stopped at their table, hand on her hip. “Show time,” Dean alerted him, speaking out of the side of his mouth as he reached for his pint glass again.

“ _Hi,_ ” she greeted breathily. She looked him up and down, a smile plastered on her face. “What’s _your_ name?” She asked in a flirty tone, her attention on Castiel.

He took a sip and when he noticed Cas wasn’t answering any of the questions she asked, Dean responded loudly, “CAS!” He startled the brunette, who just stared past the tan, leggy woman. “His name is Cas. What’s your name?”

“Chastity,” she replied proudly.

“Chastity? WOW.”

She affirmed with a high “Mmm-hmm.”

“Is that kismet or _what_ , buddy? Huh?” Cas responded by beginning to hurriedly drink his beer. After a little more sweet-talking from Dean, Chastity reached down and grabbed one of Cas’ hands.

“Come on baby,” she coaxed, pulling him to standing.

She began to lead him away but Dean stood suddenly, and grabbed his arm. “Oh, hey. Listen,” he began and Chastity fell back towards the doorway watching the two amusedly, “take this.” He thrust a folded handful of fifty dollar bills at Cas’ chest. Cas could only meet Dean’s eyes briefly while he talked, darting down to the money, then out to the brothel around him.

He advised, “If she asks for a credit card, NO. And just stick to the basics okay. _Do not_ order off the menu. Go get her, tiger.”

Cas stood there, the frightened look on his face remaining, and he swallowed painfully. “Don’t make me push you,” Dean warned, a smug smirk on his face. Cas took the money from Dean’s outstretched hand, and turned to Chastity.

He watched as the trench-coated man retreated momentarily before his gaze was torn away, following a _very_ amply-endowed woman wearing a black fishnet teddy with pink lace trim. Some minutes later, he heard Chastity scream.

As Dean left the blonde he’d chatted up to investigate, he heard her yell, “ _Get out of my_ _face!_ Leave me alone! _BASTARD_! Screw you, jerk!” She threw a plastic water bottle at Cas in the hallway, which missed his head and bounced off the nearby wall.

“I’ll kill you!” She snapped, hands clenched into fists at her sides as she shook with anger. She turned; her lips curled into a snarl and yelled in Dean’s face, “ _Screw you, too!_ GOD. Oh!! JERK!” With that she stamped down the hall, away from the two men.

“ _What the hell did you do?_ ” Dean asked, genuinely confused, stopping in front of the man, his eyes retreating back to Chastity.

“I don’t know,” Cas responded, looking after the irate prostitute’s quickly disappearing form. He was disheveled from their brief encounter: his trench coat was pulled half off from one side, revealing the black of his suit jacket; his blue tie had been loosened, and the top three buttons of his white shirt were unbuttoned.

He shook his head and responded, “I just looked at her in the eyes and told her it wasn’t her fault that her father, Gene, ran off.” Dean’s eyebrows rose higher with every word the man spoke. Cas continued, “It was because he hated his job at the post office.”

Dean broke his gaze, shaking his head disbelievingly, his lips starting to break into a smile despite himself. “Oh _no_ , man!” His eyebrows were still knit in worry however, and Cas turned his attention back to Dean.

“What?” Cas asked.

“This whole industry _runs_ on absent fathers! It’s - it’s the _natural order_ ,” he explained with conviction, trying to make the angel understand. He grabbed Cas’ arm as the bouncers approached down the hallway. “We should go. _Come on_!” Once they ran out the fire exit, they stopped side-by-side in the alley.

He started laughing, and it grew in intensity until Dean was doubled over. “What’s so funny?” Cas asked.

“Oh… nothing,” Dean replied still chuckling, clapping Cas on the shoulder as he stood. “ _Whew_ … It’s been a long time since I laughed that hard.” He put his arm around Cas’ shoulders momentarily as they walked, Cas grinning at Dean awkwardly. Cas passed in front of him to head towards the passenger side of the impala, and Dean clapped him on the back. “It’s been _more_ than a long time…years.” Dean looked off into the distance, his smile slowly falling.

\--------------

  

As they drove on, Dean became more and more aware of Cas’ unwavering gaze. Those two sentences kept whirring around in Cas’ mind: ‘This whole industry runs on _absent fathers_. It’s the _natural order_.’ His mind went over other conversations they’d had, trying to get a grasp on some coherent train of thought.

A few hours passed this way: Cas staring out the window, or alternately, at Dean. Dean hit the power button on the stereo and it went black. “Hey Cas, can I ask you something?”

“Of course, Dean.”

“I probably should’ve brought this up before, but I was a little distracted…”

“With the prostitutes,” Cas supplied.

“…Yeah. So anyway, how does this vessel thing _work_? Is Jimmy inside your noggin, yelling at you for letting me drag you to a brothel?”

“No, he’s not. Jimmy Novak… we’ve made other arrangements.”

“Oh, yeah?” Dean had to hear this.

“In exchange for the use of him as a vessel and the safety of his family, he’s asked to not be present in my affairs.”

“Okay, you lost me.”

“When an angel enters a vessel (assuming the angel is not an archangel, that is), one of three things can happen: either the soul demands to be conscious while their body is being used, they ask to move on, or they wish to maintain occupancy without consciousness. Many things angels do can be… troubling to humans, and they wish not to see it. In this case, a very deep dream-like state is entered by the soul, so that an angel’s grace may more fully command the vessel.”

“And Jimmy picked the last one?”

“Not at first. Initially, Jimmy demanded to command his body alongside me. Our consciousnesses battled and he was disheartened by some of the tasks I was made to complete. As a devout man, he understood this was God’s will, and that I am an extension of that. After a while, he requested to sleep. He said that he trusted my judgment and that whatever I did, I wasn’t to tell him. He said it didn’t matter as long as it brought me closer to my aims, whether it was serving Heaven or protecting the Winchesters. I was only to bring him to his family when this was over.”

Dean nodded, and replied, “So you didn’t screw it up with Chastity on purpose?”

“No. I wasn’t aware you weren’t supposed to bring up a prostitute’s father.”

“Yeah… that sorta thing can be a real sore spot for them.” Dean swallowed, and looked over at Cas. “Okay, good talk.” He clapped Cas on the shoulder, and turned the radio back on.

A few more hours passed, and Dean steeled his jaw, his thoughts an unfocused jumble. He gave a small nod, more to himself than to his friend. “Cas, we’re going to be making a pit-stop.”

“Why? Shouldn’t we be heading back to trap Raphael?”

“That dick can wait a little while longer.”

Dean turned off onto the next exit, and they soon found themselves in front of a motel. “Wait here. I’ll be right back.”

He came back a few minutes later, and gestured for Cas to follow him. They walked side by side in silence, and Dean stopped in front of room 20. Cas eyed the blue door curiously; Dean had a habit of always choosing this number if he had the option. After they passed through the doorway, Dean locked the door behind them, and drew the thick twill curtains tight. He shrugged off his jacket and slung it over the back of the chair near the door, before he sat down on the lone queen-sized bed, kicking off his dusty work boots. Castiel just stood nearby, watching him intently. Since he’d agreed not to read Dean’s mind anymore, he was utterly confused.

Dean peeled off his socks, and began unrolling the cuffs of his faded green over-shirt. “Sit down. You’re making me nervous.”

Cas just nodded, perching on the edge of the bed with his hands resting on his knees. He watched as Dean shrugged off the garment, clad only in a black t-shirt and faded jeans now. His eyes flicked to Cas momentarily, and he licked his lips nervously. Cas’ eyebrows drew up in confusion, his mouth set in a thin line as he watched the elder Winchester attempt to collect himself. Dean’s fingers fumbled to remove his wristwatch, and he swore under his breath. He stood up suddenly, and pulled the comforter out of its hospital corners, his hands slightly trembling. He rooted around in the duffle he’d dropped unceremoniously near the head of the bed, dropped his watch into it and looked over his shoulder at Cas.

“Make yourself comfortable,” Dean advised, looking at a point just beyond Castiel, “we got another thousand miles to drive tomorrow.” He stood up momentarily and stretched his back, gaze turning to the angel still perched near the foot of the bed. “I’m gonna hit the head.”

Castiel watched Dean disappear into the bathroom, then looked around the room: the motel was nicer than the ones Sam and Dean usually stayed at, but that had been sheer luck; it was the only one around for miles. He took in the soothing shade of green on the walls, and the deep blue of the ceiling. He supposed the owners were going for some sort of aquatic theme, if the angelfish-shaped keychain was anything to go by. The comforter he sat on was a thin, quilted number, a night sky reflected in a still ocean printed upon it. Dean had inexplicably switched on the lamp switch before he shut the door to the bathroom. His eyes travelled to the lamps on either side of the bed; the pyramidal shades dimming the light significantly, they cast a flattering glow on the dark wood surface of the nightstands upon which they sat. The room was almost too bright now, the ceiling fan’s bulbs blazing brightly. Usually, things that were annoying to humans such as sensory overload didn’t bother Castiel. However, he reasoned with himself that today had been an _unusual_ day, and that seemed to settle the matter in his eyes. With a snap, the overhead light went dark.

He took a deep breath, suddenly more content in the foreign room. He let his gaze roam to the seahorse-shaped magnets on the fridge just beyond the bed. It was a small refrigerator, and sat in the hollow of the entertainment center which housed a modest television. A pamphlet on one of the nightstands advertised “Casa Erotica 12,” the TV remote covering the woman’s form.

His eyes went to the plush blue carpeting. It looked soft and by the strangely plastic smell of the room, had been recently laid. As his eyes continued to sweep the room, his thoughts began to wander from his surroundings. Dean had already driven them thousands of miles to try to do Cas a favor – the least he could do was let Dean sleep. He realized in some far-off part of his brain that humans required it. He supposed Dean had a point earlier: they had a long way to go to get back to Maine, and the ritual _had_ to be performed at sunrise; It just wouldn’t be _this_ sunrise.

Dean, meanwhile, was having a minor freak-out. After using the bathroom and washing his hands, he looked up at the mirror, trying to psych himself up. _Come on,_ he told himself, barely recognizing the anxious man staring back at him. _It’s_ _not that big a deal._ He took a deep breath, schooling his expression into something indifferent. _Not like you’ve never done it_. He sighed, releasing his grip on the sink and splashed some cold water on his face.

He could do this.

 

He emerged from the bathroom, sat back down on the side of the bed, and patted the spot next to him. He noticed the room had gotten much darker, but said nothing. It would be easier this way. “I made you a promise,” he reminded the man. Cas moved over, going over every conversation Dean had ever had with him in his mind.

The confused look remained, and Dean sighed heavily. “I told you I wouldn’t let you die a virgin.” The two gazed at each other for a minute, Dean shrugging his shoulders back.

Dean reached out and wrapped his hand around Castiel’s tie, pulling him close. Before he lost the nerve, he closed the distance and met his lips. Cas’ lips were softer than Dean had expected, and he noticed how different it felt to kiss naked lips. When the kiss ended, Dean opened his eyes. Cas no longer looked confused, but now wore the frightened expression he’d had in the brothel. He tried painfully to swallow, while Dean met his eyes. “I keep my promises… _okay?_ ” They both recognized the request for what it was, and Cas knew he had two choices: fly away and wait for Dean in Maine, or accept what his friend was offering.

Cas blinked, then grabbed the lapels of his trench-coat and pulled it off, the tan material fluttering as he cast it aside. Dean undid the loose knot of his tie before slipping it off. He pushed the suit jacket off of Cas’ shoulders, and gathered the garment in his hand. Dean tossed these on a nearby chair, waiting for Cas to make the next move.

He could feel his heart beating in his throat, his mouth going dry. Dean moved his hands to the bed, his fingers digging into the bedding to control his nerves. _No, you can’t treat this like it’s real. Pretend he’s one of them._

Dean was pulled from his thoughts by the sight of Cas’ hands. They met the edges of his collar and travelled down, his fingertips unconsciously brushing his chest. Cas’ fingers worked at the remaining buttons of his button-down efficiently, and he shrugged it off. The muscles in Cas’ bare chest twitched and jumped as he threw his shirt toward the chair. Dean took in the sight of his tanned skin, his torso a combination of flat planes and lean muscle. He wanted to run his thumbs over Cas’ sharp hipbones, wanted to press his lips to the hollow of his collarbone. He felt himself hardening, and he took another deep breath to control himself. _It’s about him, not about you._

He watched as Dean pulled off his t-shirt by the scruff of his collar, and began working on his belt buckle. Cas’ eyes moved from the anti-possession tattoo under his clavicle to the pink, erect nipples underneath and finally to his hands at his waistband. After Dean had unbuttoned and unzipped his pants, he reached towards Cas.

It was at this moment he realized he was a participant, and not just an observer. He looked nervous now, and glanced towards Dean’s duffel, the purple tube of lube visible next to a roll of condoms. Dean’s eyes followed his, and he turned on a sly smile: “Don’t _worry._ I’ll take care of you.” Despite Dean’s confident assurance, Cas gripped the comforter tightly, his arms bent on either side of him.

_Show him you_ _mean it._

His hands went to Cas’ chest and slowly travelled down, his calloused fingers skating over the smooth skin and stopping at the waistband of his slacks. His fingertips splayed along his stomach and he could feel the fine trembling of Cas’ muscles, the hairless skin there practically jumping from the contact. He undid his belt quickly and snapped the button open before leaning forward again to catch the angel’s lips with his own. He kissed harder, more insistently until Cas’ lips parted in an unheard sigh. His tongue peeked out and gently caressed Cas’, his lips pliant. After a few minutes he drew back, his lips still tingling. His eyes met Cas’ again as his fingers dragged the zipper down, feeling the slow hardening of Cas’ cock through the fabric.

Dean drew back and shifted his hips off the bed, pushing his jeans and underwear down in one go. His sudden nudity seemed to fluster Cas slightly, although he still said nothing. “Lay down,” Dean ordered, and Cas complied, reclining against the bed. His hands seemed to relax their grip on the bedding at this point, but his breath was still shallow, apprehensive.

He dragged Cas’ slacks and underwear down, cursing when he noticed they were impeded by his shoes. He pulled off the shoes and socks quickly, and then yanked the pants free, and everything lumped together on the floor. As his gaze made its way back up Cas’ body, he found his thoughts taking a dangerous turn, and he struggled to resist their allure.

_No. This is just a favor, that’s all…_

Dean blinked rapidly, clearing his head. He crawled up onto the bed to the side of Cas, and leaned over to get the lube from his duffel with his right hand. He clenched the muscles in his arms, willing them not to shake as he righted the bottle. He knew this part would be the hardest. Dean was used to Cas staring at him by this point, although it had never been with this intention. His cock twitched at the thought.

Eyes still on Dean, Cas watched as the top was snapped open, the vacuum-sealed click breaking the silence. He felt strange, but it wasn’t unpleasant: his heart was racing, his mouth was dry, and his penis felt different. As Dean dripped the lube onto a few of his fingers, rubbing them together to warm the gel, his focus shifted to Dean’s body. Up until this point, he hadn’t gazed any lower than Dean’s navel for more than a second. Now, he let himself look: Dean’s body was softer than Castiel’s – it looked more inviting. Cas found himself wanting to run his hands up and down Dean’s muscular thighs, and then… he panicked: They were two men. How were they going to–

Cas’ thought was interrupted by the sight of Dean’s next action: Poised on his knees, he reached his lubed fingers behind himself, and bore down; with a groan, he forced two of them inside. Dean panted, his face screwed up in discomfort as he began to work himself open. His legs trembled, his hole burning at the sudden intrusion. “B-been awhile,” he admitted, his voice shaking. He cleared his throat and took a deep breath; he had to relax. _He needs you to teach him._

Dean reached forward with his other hand and began to stroke Cas’ half-hard cock. He felt it pulse beneath his fingertips as it stiffened, and he bit back a moan. He felt his breath go shallow and he dragged his eyes regretfully upward to get a gauge of Cas’ reaction. When he noticed Cas staring at him with concern, he attempted a small smile, and remarked, “Just like riding a bike. Almost there.”

He worked his fingers in earnest, his fingertips making contact with his prostate. His breath puffed out suddenly, and his cock gave a twitch. Having stroked Cas to full hardness, his hand reached toward the lube again, and he removed his fingers. _Oh, fuck._

What was he getting himself into? He stared at Cas’ cock, his mouth going dry again. He hadn’t been worried when Cas was only at half mast. But Cas was a “grower” and had to be almost eight inches. He didn’t look too thick for Dean to take, but he wasn’t sure when the last time he’d had something this big in him was. He felt himself clenching involuntarily, and he drew a shaky breath.

Suddenly, a remembered quote reverberated in him: “Such a _greedy little cock-slut_ , aren’t you?” the man had asked as he pushed into Dean’s tight, young hole. He’d made doe eyes at the man after a groan had left his throat and nodded to keep from crying out.

The unwanted memory had been exactly what he needed to get in the right head-space. He’d been struggling with what _this_ was, but that was over; he knew his place now. He took another deep breath, this one steady. He re-lubed the digits and added another before he pushed them in again, groaning anew. His fingertips found his prostate quickly, as he attempted to distract himself from the burn of the sudden stretch. He reached his other hand towards his duffel again and pulled up the condoms. He ripped one free and tossed it at Cas. “Here, put this on.”

Cas asked simply, “Why?”

He swallowed painfully, and broke his gaze momentarily as he answered, “You don’t know where I’ve been.” He’d said it lightheartedly, but the look in his eyes betrayed the smile on his face. The look Castiel gave Dean in return was heartbreaking. Dean tore his eyes away from those sad blue ones and added, “It’s been a few months since I’ve been tested. I don’t wanna give you anything.”

_Could you be any less sexy?_

Cas wanted to point out that it wouldn’t matter if he died tomorrow, but felt this might be the wrong moment to make that statement. Instead he nodded, and tore open the foil packet. “Guess I’m not as on the ball as I used to be,” he remarked more to himself than Cas. He watched as Cas rolled the condom onto himself, and then looked back up at Dean. He withdrew the fingers from himself, and reached for the lube again. He slicked Cas up and straddled his thighs. _Oh God. This is actually going to happen._

“Hold it steady,” he directed, and Cas complied. Dean lined his cock up with his hole, and did his best to relax. The heartbreaking look remained, and Dean added, “And stop looking at me like that. I’m trying to do you a favor.”

_Fuck him right and he won’t care what you said to him before._

Dean slowly lowered himself down onto Cas, moaning loudly at the intrusion. He couldn’t help it – that always happened when he took a cock. When he met Cas’ lap, he leaned forward, panting slightly. He needed time to adjust, so he stalled: “There isn’t anyone on either side of us. Make as much noise as you want.”

Cas just nodded in response, and Dean leaned back, planting his hands on either side of him. As he began to roll his hips, he coaxed a small groan out of Cas. He soon found a rhythm that pulled more sounds from Cas, and he smiled at the way he was slowly unraveling the angel’s control.

His cock ached painfully – he hadn’t touched it once since they started. He wanted to beg Cas to touch it. Dean _wanted_ and _yearned_ down to his core for Cas to touch him, to taste him, to hold him. But he knew he couldn’t ask that. And he hadn’t touched himself for fear of going off like a damn teenager. He focused on the feeling of Cas’ cock stretching him wide, his eyes fluttering closed. He concentrated on the pressure of the head of Cas’ cock glancing that special spot inside him, and he let out a small keening sound.

He reached out tentatively, gently gripping Dean’s hips, and Dean’s eyes flew open. Dean closed his hands over them; “You can be rougher, you know. I won’t break.” He moved his hands to Cas’ chest, his fingers brushing over his nipples experimentally. When this elicited no response, he reached between his legs to gently pull on his balls. Cas had unwittingly been hitting his prostate, and he was beginning to feel that buzz deep in his core. _Give him a show._

Despite how good it felt to stay in the position he was in, he shifted his legs to give Cas a better view of where they were joining. Cas finally broke his gaze from Dean’s face and stared at his cock as he made small, hesitant thrusts up.

“That’s so good… _More_ ,” Dean begged, forcing his face not to screw up; they usually liked the slack-jawed look. Cas started moving faster, and Dean reveled in it. This, Dean _knew_. This, Dean was used to, and he slammed back down onto his lap repeatedly.

_Yes. Use me._

But as Cas met his gaze again, his pace flagged: Dean’s eyes were… empty. His face was blank, and he bit his bottom lip in concentration as he rolled his hips. Cas wrapped his arms around Dean’s back, and pulled him closer.

Dean’s sudden look of panic was quickly hidden by a “come-hither” expression, but not quickly enough. “What’s wrong?” Cas asked, not moving.

He struggled to pick up the slack from this position and replied, “Nothing, just haven’t… been this close before.” He looked away again, an unreadable expression in his eyes. “Let me up, Cas. You can’t really fuck me like this.” He struggled under the angel’s strong grip. He wasn’t scared, but what he did feel was even more terrifying. He chastised himself: _You’re convenient. That’s it._

“So?”

“Cas, let me do this for you. If you don’t like it, there’s no _point_.”

“I like it, Dean,” he replied. As if to illustrate his point, he rolled his hips up into Dean, his thrusts slow but forceful. The feeling jarred Dean from his thoughts, and he let out another moan.

“You like doing it like that?” Dean asked, an idea forming in his mind. His lips curled lasciviously and he purred out, “Get me on my knees and you can go in deeper.” If Dean was biting a pillow, he wouldn’t have to see the way Cas was looking at him.

“No,” he replied, his cerulean eyes gazing entreatingly “Stay here with me.”

“I am –”

“Mentally. Don’t retreat, Dean. _Please_ , I won’t hurt you.”

Dean was stunned, and lay against Cas, braced on his elbows. If this was what Cas wanted…

“You need to do this right as much as I do. Stay with me, Dean.”

With that, he rolled his hips again, glancing his prostate. He clenched in waves, his body drawing Cas further into him. He shuddered at the feeling, grinding forward to get more friction on his untouched cock. Dean finally met his eyes again and Cas saw the vulnerability there; coquette Dean was gone. All that remained was this scarred man letting himself be weak.

He clenched around Cas, reaching out for his hand. When he found it, he twined their fingers together. “ _Cas_ ,” he moaned, feeling himself on the edge. Cas gripped his hand, and thrust faster.

“Dean,” he responded, getting close himself, “it’s okay.”

With a strangled groan, Dean came. As he felt it shoot out of him, sparks washed over his vision, a sobbed moan of the angel’s name passing his lips again. He blinked, gazing down at the blue eyes below him. He clenched weakly, his legs shaking as he rode it out, and slowly came back down to reality.

Cas’ eyes squeezed shut and he breathed out a “ _Dean_ ” before losing his voice to ragged pants. He pulsed, his hips jerking of their own accord. They slowly stuttered to a halt, and Dean leaned back, straddling his lap. The urge to curl up in Cas’ arms was almost overwhelming. He took a deep breath, relaxing his hole. He braced himself against Cas’ chest with one hand, the other hand holding the base of the condom down. He shifted up, pulling the spent cock out of him.

He moved, rolling off of Castiel and standing up. He walked awkwardly to the bathroom, leaving the disheveled angel looking slightly dazed on the bed. After using the bathroom he washed his hands, keeping his head resolutely down; he couldn’t look at himself right now.

When he came back into the room, he felt Cas’ gaze on him. He noticed Cas had mojo’ed himself clean while he was away, and had found his underwear to boot. Dean stepped into his boxers and was searching for his t-shirt when Cas said, “Dean.” Dean’s shoulders flinched imperceptibly but he just pulled on the shirt, back now to the angel.

“ _Dean_.”

“Yeah, yeah, you’re welcome. Just don’t tell Sam, okay?”

“It was very pleasurable.” Dean smirked at this, and let out a full-body yawn.

“Dean, look at me.” Dean turned around slowly, and met Cas’ gaze.

“Yeah?”

“You’re upset.”

“Nah, I’m fine.”

“You’re experiencing regret.”

“What I’m ‘experiencing’ is exhaustion. I’ve gotta rest, man. Wake me up in four hours, and we’ll hit the road.”

“I’ll watch over you,” Cas agreed, and got off the bed. He had managed to find his boxer shorts while Dean was in the bathroom, but was otherwise naked. He watched Dean get under the covers and he murmured, “Get the lights, Cas.”

Cas turned off the lamps with a snap. He thought he heard Dean mutter a “thanks” but couldn’t be sure. He picked up his articles of clothing from where they’d been flung but seemed reluctant to put any of them on. Cas gazed at the clock and noted the time, before letting out a large sigh. Slowly, he picked up his socks…

The next four hours seemed to fly by. When Cas touched Dean’s shoulder, the man jolted awake. “Sammy?” he called into the darkness, his voice hoarse from sleep.

“Sam’s not here Dean,” Cas reminded him, and withdrew his hand. Dean looked around, and realized the room only had one bed in it. He clicked on the lamp beside him and stared down at his phone.

“I slept more than four hours?” he asked, incredulous.

“Five. Your r.e.m. cycle wasn’t over. It would’ve been unwise to wake you.”

“How did you – did you go poking around in my brain again?” Dean asked accusingly, and Cas just stared back at him wearily.

“No. I monitored your eye movements.”

Dean still seemed too sleepy to argue properly, so he just nodded. As he sat up, he rubbed the sleep out of his eyes and yawned. He stood up slowly, shuffling around the room to gather up his clothes. As he yanked on his socks he asked, “Where are your pants?”

“Tonight was the first time I’d been without clothing since inhabiting this vessel. I enjoyed the feeling.”

“Right… Well, you need to get dressed now. We have an archangel to snag.” Cas squinted at him for a few moments, then gathered his clothes from the table he’d set them on. He pulled on his slacks. Dean zipped the duffel close, and shoved his phone in his pocket. While he waited for Cas to finish getting dressed, he buttoned his over-shirt, and found his jacket across the room…

                                                                                                             ______

As Dean started the impala and peeled out of the parking lot, Cas said, “For what it’s worth, I don’t think any less of you. You did what you had to do to keep you and your brother fed and sheltered.”

He tightened his grip on the steering wheel, setting his jaw. “I don’t know what you’re talking about, Cas,” he lied, turning on the radio. Cas waved a hand and the radio fell silent. A steady rain was beginning to fall against the windshield and the sound was thunderous in the stretch of silence that followed.

“Dean, we are about to go up against an archangel. If your mind is _anywhere else at all_ when we get there, he will use it against you to turn you into the Michael sword. We will talk about this _now_.”

Cas squinted at Dean, and he nodded his assent. “What you did… it wasn’t out of lust or greed. It was out of love. So, to me at least, it was not a sin.”

“Doubt your pops sees it that way,” Dean replied, trying to lighten the mood. His stomach was actually churning painfully, talking about _this_ with a freakin’ _angel_.

“I do not wish to abuse your trust: I didn’t just figure this out tonight, but it did give me some context.”

“Wait… _you knew_?!”

“You have nightmares… often. When I watch over you, you sometimes wake in the middle of the night. At first, I would simply put you to sleep – a dreamless sleep. But the longer it went on, the more I worried. I worried that your time in hell had shattered your psyche to the point that you might do something rash. I sought to understand… I’m sorry Dean, but I read your mind while you slept. I saw your nightmares. Mostly they were flashbacks to hell. But once, I saw something older… Something from your childhood: The man in the alley the first time you went down on your knees, and…” He took a deep breath to collect himself, thinking about how to phrase it. “And the other man, the first time you –”

“ _Enough!_ ” Dean cut him off, the force of his outburst startling the angel.

“I get it, you gate-crashed my head and watched guys fuck me. Point taken,” he replied, eyes focused resolutely on the road.

“Dean, I did not watch because it gave me pleasure. I wanted to understand your pain. Besides, the bad moments were not the only memories I witnessed. Occasionally your mind would drift to something more pleasant, as a way to self-soothe. I also saw the first time you bought groceries when your dad’s money ran out. I saw the first time you got off your knees and bought another week at the hotel. I saw the way your cheeks began to fill out because you no longer had to go without to make sure your little brother could eat. Dean, I know why you pick number 20.”

Dean flinched, not sure he wanted to hear this.

“You were twenty years old when you were able to stop for good. That was the year Sam turned sixteen. That was when he was old enough – and you trusted him enough – to get an honest job. I know you only did it when you absolutely had to; when you needed to eat or to pay a bill… that was your only skill set.”

_Jeez… how many dreams had the guys stepped in on?_

Dean took a deep breath: “Yeah, okay? I was a snot-nosed kid, and when I was sixteen I couldn’t hustle pool or gamble to save my life. I stole from people now and then… but lifted pocket change won’t cover a meal, and the only time I ever shoplifted, I got arrested. We moved around so much that Sam and I never got free lunch at school, even though we sure as hell qualified. We didn’t really have any friends besides each other, so it’s not like we could just go somewhere else for dinner. Dad was always too busy with ‘the job’ to teach us how to feed ourselves or how to buy groceries. He taught me how to heat up beans and dial for a pizza, but that was about it. And it’s not like we coulda learned from example: the old man seemed to run off of cheap beer and sandwiches.” He bitterly recalled a memory of John feeding them fried bologna sandwiches and passing out in front of the TV, while Sam just cried because he was running a fever. Thank god he’d been old enough to open child-proof caps.

He took a deep breath, changing track. “But you didn’t ask about how poor we were as kids. You wanted to know about the tricks, so I’ll tell you. There were no women. You can’t get women to fuck you for money when you’re under-aged. I was 16 when I blew a guy for the first time. I got thirty dollars, and I remember thinking how _easy_ it was. When I was that age, I hadn’t really filled out yet. I was strong, but I was lanky – you know, a twink. Back before I could grow a beard, I looked a lot more like a girl, which they liked. I wore my clothes baggy, and that year I let my hair grow longer. My voice hadn’t finished changing all the way, so if I really tried, I could make it high. Most of the guys I went down on didn’t know I was a dude.” He smirked, shaking his head. Cas had a hard time believing it, as well – he’d never considered Dean as anything other than the man that he was.

“But after awhile, that didn’t work anymore. My voice got deeper, and I started to pack on muscle. I was still kind of twinky-looking, but everyone knew I was a boy. So I had to get creative. I wore eyeliner and tighter clothes to attract the guys I knew for sure were queer. We spent a year in this town and all the locals at the bar were getting to know me. They knew I was good for a back-alley bj, but one a week wasn’t paying the bills. And dad sure as hell wasn’t paying them. We lived in a shitty motel that only took cash, so it’s not like his fake cards would work. But at that point he was convinced that we were old enough to handle ourselves, so he could focus on what was ‘important’.” He sneered – Sam was fucking _twelve!_

“Bobby tried to help the few times I called him, but dad found out and smacked some sense into me. He told me I was making him _look bad_ , that we didn’t need any ‘fucking charity’. He rented the hotel for another week and threw 50 bucks at me, then left again. But one week turned into two, and the money ran out like it always does. I needed more – a lot more. Since it turns out guys can’t charge as much as girls, twenty dollars wadded up in my hand after I spit some guy out didn’t buy Sammy new shoes or a winter coat.” He took a deep breath, and the next bit came out fast. “So, uh, three days after my 17th birthday, I let a guy bend me over in his hotel room. I knew how to fight better by then, so I knew I could handle myself against a paunchy, balding middle-aged dude. In retrospect, it wasn’t that bad; he had lube, a condom, and just wanted some strange. It hurt like a bitch after, though. I didn’t know you had to prep yourself, that you had to relax. I didn’t expect a reach-around or anything, but this guy was pretty nice for a trick. And I left with 100 dollars, so what did it matter?” He took another deep breath, and tightened his grip on the steering wheel.

“I – I can’t talk about it anymore, though. If you wanna know, just… see for yourself.” He gestured to his temple, giving Cas permission to read his mind.

Cas pressed two fingers to Dean’s temple, and a wave of Dean’s memories assaulted him. Dean braced against a cold brick wall in a muddy alley, some hairy biker plowing into him and calling him a dirty whore; Dean and another man in a hotel room, the man spitting into his palm for lube while Dean got down on all fours; Dean in the backseat of a car, riding some middle-aged man like he actually enjoyed it… he had.

Dean getting shorted after another alleyway quickie, and being too sore to chase after the dirt-bag; Dean taking a scalding shower in the middle of the night and trying hard not to cry, a thin trickle of blood dripping down his leg.

Cas saw the bike Dean bought Sam; the new school clothes and the money order for Sam’s SAT test; the thickly-lined coats to combat the Midwest winter; the stocked fridge and the marks on the door frame showing how much Sam had grown.

But he also saw the confused looks Sam sometimes gave Dean: The sleepy confusion when Dean hadn’t slipped into the room quietly enough; the alarm when Dean awoke with a giant bruise he hadn’t had when they’d gone to sleep that night; the skepticism when Dean said he’d won the money at poker, or hustling pool; The worry when he walked in on Dean in the bathroom: he had the toilet lid down and was sitting on top of it, dabbing rubbing alcohol onto his scraped-up knees. The both knew Dean was lying when he’d said he’d gotten into a fight, but neither said anything else. He prayed Sam never figured it out.

Of course, Dean had been getting better at pool and poker during this time, so it wasn’t a _total_ lie. And after the time Dean had gotten hurt… down there, he stopped for a long time. He’d had a tiny bit of dough squirreled away in a sock in the bottom of his duffel bag. After new cash stopped flowing in, he began to dip into it, little by little. Sam hadn’t noticed, at first: Dean just went grocery shopping less often and stopped buying things they didn’t absolutely need. After a month of spaghetti-O’s for dinner though, he said, “I should get a job.”

“No, Sammy. You go to school. _You’re_ the smart one. Besides, you’re only fifteen – you can’t get a job anywhere.”

“I can get a work permit, work after school _. It’ll be fine_ , I don’t need to study as much as I do…”

“God dammit Sammy, I said NO! _I’ll_ get us money. You just keep your nose in the books.”

After that, Dean had started giving head again. But he was wary, and hoped this would be enough; it wasn’t. After Dean lost his last twenty dollars to a pool shark and John had called to say he’d be gone another week, he resigned himself to his fate. He took another guy in the alleyway and used the money to buy more lube and condoms. He couldn’t always make the tricks wear one, especially if he needed the money bad enough. But he could have proper lube on him and start prepping himself before his nights out again.

So the last year was the hardest: he worked at a garage during the day, slept for a few hours, and went out at night. He hustled pool and gambled, but when he lost, he hooked in the back alley, or the bar restroom. He saved as much money as he could, but he got thin again from the stress of it all. And sometimes, it was easier to not eat than to bend over. He got checked out at the local clinic from time to time; he’d only gotten Chlamydia once from oral sex, thank god. As shitty as it was, he thanked his stars he’d never gotten anything worse.

Dean’s memory went to Sam’s sixteenth birthday, and the announcement that he’d gotten an after-school job at the local bowling alley. Dean was worried, but Sam juggled both school and work with finesse. He started putting on weight from working around greasy food, and muscle from lifting heavy equipment all day. By the time Sam left for college, he was in his beginning stage of Sasquatch-ness.

Dean’s memories faded after that, and Cas broke the connection between their minds. He lay back against the passenger seat, and just stared at Dean for a long time. When he finally spoke again, his tone was more serious than Dean had ever heard it. “ _Dean_ –”

“Just… leave it. It’s the past; there’s nothing we can do about it.”

They drove in silence until they were back in Maine.

“Dean?”

“Yeah Cas?”

“I’m glad it was me, and I’m glad it was you.”

“What?”

“I’m glad I was the one to save you from hell. And I’m glad I lost my virginity to you. I didn’t care for Chastity.”

“Come on man, she was hot!”

“No, you misunderstand. I didn’t _care_ for her,” he emphasized.

Dean’s mouth crooked into a smile. “I like you too, Cas.”

                                                                                                    _______

It was as if the impala was a space separated from the real world. When the men pulled into the parking lot of the hospital, the spell was broken. Everything terrifying and real and sacred that had been said inside would stay there. As they made their way to the front entrance, something shifted. Once again, they were hunter and angel, and they had a job to do.

 

The sun began to rise behind Castiel. Dean shut the blinds of the room at St. Pete’s and Cas poured a circle of oil around Raphael’s last vessel – Donnie Finnerman. Dean fingered the box of matches in his pocket, and tossed them to Castiel. Nodding towards the window, he said, “Show time.”

                                                                     _______________________________________________________________

 

 

 

**Author's Note:**

> I think this is the saddest thing I've ever written. Even so, I hope you liked it.
> 
> As always, kudos and comments are always appreciated. Thanks for reading.


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